How NOT to Run a Startup in 10 Easy Steps
I’ve been lucky (or unlucky) enough to have a front row seat as an early employee at four different AdTech startups. I lived through two exits and one to later go public, several near-death experiences, and many ups and downs. Through my experiences, I’ve learned some things about the activities and actions that can make or break a startup.
Advice should always be taken in context and applied to your unique situation, but I’ve been exposed to enough situations where I’ve seen clear patterns emerge. Patterns that I also innately believe. It’s usually not one single mistake that kills a startup. More often, it’s the daily habits and lived culture (not stated) that compound over time.
I hope this list can help someone out there building something meaningful.
This is How NOT To Run a Startup In 10 Easy Steps...And What To Do Instead
1. Don’t be honest with your investors
Hide the hard stuff and assume investors won’t notice.
What to do instead: Be transparent. Good investors want the truth so they can help with advice, intros, or resources.
2. Overpromise at every board meeting
Inflate projections and hype “the next big customer” that never signs.
What to do instead: Share realistic milestones. Momentum and credibility matter more than exaggerated stories.
3. Focus only on pipeline
Chase meetings like they’re revenue. A busy calendar isn’t traction.
What to do instead: Balance pipeline with product-market fit. A few paying customers beat a hundred dead leads.
4. Let customers dictate the product
Pivot with every discovery call and build a Frankenstein wishlist.
What to do instead: Listen, but keep conviction in your vision. Feedback sharpens your strategy, but it shouldn’t replace it.
5. Treat every employee like a salesperson Push everyone to sell, even if they were hired to build, design, or support.
What to do instead: Let sales sell and builders build. Growth only scales when each role does what they do best.
6. Sell to anyone who will listen
Spray and pray. Pitch to anyone with a pulse.
What to do instead: Define your ideal customer and stick to it. Focus brings clarity to both product and pitch.
7. Micromanage your senior employees
Hire leaders, then second-guess every decision with endless check-ins.
What to do instead: Trust the people you hire. Your job is to set direction and clear roadblocks, not be involved in every decision or interaction.
8. Treat every relationship as transactional
Max out what you can extract from every customer, partner, or employee.
What to do instead: Play the long game. Provide value first and watch relationships compound over time.
9. Believe your startup is the center of the universe
Blast out filler press releases and post daily fluff on LinkedIn.
What to do instead: Share updates that matter: customer wins, product launches, and real insights. Substance earns attention.
10. Take credit for successes, blame others for failures Hog the spotlight when things go right, point fingers when they don’t.
What to do instead: Celebrate your team and own your mistakes. Accountability is what real leadership looks like.